Southwest Side Vacation Packages 2026 from $376

Southwest Side flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$376

per person

Mar 4 - Mar 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$614

per person

Mar 7 - Mar 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$498

per person

Mar 7 - Mar 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

theWit Chicago, a Hilton Hotel

Downtown Chicago

Save 100% on your flight

$543

per person

Mar 7 - Mar 12

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$456

per person

Mar 4 - Mar 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Top Southwest Side hotels deals

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$164 nightly

$192 total

Jan 11 - Jan 12

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Pool

Hot Tub

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$105 total

Jan 8 - Jan 9

Total with taxes and fees

A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$168 nightly

$192 total

Jan 11 - Jan 12

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.

Pool

Spa

Club Quarters Hotel Wacker at Michigan, Chicago

75 E Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$103 total

Jan 24 - Jan 25

Total with taxes and fees

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-in, and express check-out are also on offer.

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$111 total

Jan 8 - Jan 9

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.

Sable at Navy Pier Chicago, Curio Collection by Hilton

900 E Grand Chicago IL

Free Cancellation

Reserve now, pay when you stay

$114 nightly

$134 total

Jan 20 - Jan 21

Total with taxes and fees

This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Marquette Park

After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Holy Cross Hospital

Though Holy Cross Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Chicago while you are here.

St. Bernard Hospital

Though St. Bernard Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Chicago while you are here.

Frequently asked questions

How much are vacation packages to Southwest Side?

Epic adventures await in Southwest Side, with Travelocity vacation packages starting at just $376. Providing both hotels and flights, these sensational deals make it a cinch to see all corners of the globe.

Where can I get the best vacation package deals for Southwest Side?

It's simple — look no further than Travelocity. With no less than 400 partner airlines and 1,000,000 worldwide properties, it's easy to put together a Southwest Side package deal that suits your travel style.

Why should I purchase my Southwest Side vacation package with Travelocity?

Whether you're searching for the ultimate unplugged vacation or you crave the hustle and bustle of the big city, booking everything with Travelocity saves you time, hassle and money. No need to sift through hundreds of websites looking for the best deal — our Price Match Guarantee ensures you'll never be out of pocket, and our team of customer service experts are available 24/7 should you need anything at all.

Can I save on my Southwest Side car rental if I book it with my hotel or flight?

Sure can. And our Southwest Side vacation packages are the perfect way to do it. With only a few clicks you can save money as well as time by booking everything in one place. Collect the keys to your rental car and feel the freedom of the open road. Searching for things to do? Add some tours or experiences to your package and make savings on those too.

Which airport is best for Southwest Side?

For anyone heading to and from Southwest Side, the most used airports are O'Hare Intl. Airport (ORD), Midway Intl. Airport (MDW) and Lewis University Airport (LOT).

What is there to do in Southwest Side?

Southwest Side boasts hidden surprises at every corner, but be sure you plan a visit to both S.S. Peter and Paul Church and Balzekas Museum of Lithuanian Culture while you're here. These attractions are very popular with visitors to the region.